5-Bromo-2,3-dihydro-1-benzothiophene → 5-Bromo-2,3-dihydro-1lambda6-benzothiophene-1,1-dione

HRID 732752Notes

Reaction equation

HRID 732752 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2S[CH2:7][CH2:8][C:4]=2[CH:3]=1.O[O:12][S:13]([O-:15])=O.[K+]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[S:13](=[O:15])(=[O:12])[CH2:7][CH2:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 123415135-Bromo-2,3-dihydro-1-benzothiopheneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 123527005-Bromo-2,3-dihydro-1lambda6-benzothiophene-1,1-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 5-bromo-2,3-dihydro-benzo[b]thiophene (J. Am. Chem. Soc, 1973, 1916-1925, 4.3 g, 20 mmol) in MeOH (100 mL) and add oxone (36.9 g, 60 mmol). Stir the reaction mixture at room temperature overnight, and then remove the solid by filtration. Concentrate the filtrate and purify the residue by flash column chromatography (silica gel, 20-40% EtOAc/Hexane) to give 4.24 g of 5-bromo-2,3-dihydro-benzo[b]thiophene 1,1-dioxide (86%).

Workup

  1. customremove the solid
  2. filtrationby filtration
  3. concentrationConcentrate the filtrate
  4. custompurify the residue by flash column chromatography (silica gel, 20-40% EtOAc/Hexane)

Sources & evidence

ORD record
ord-ada5215e62094c1396d91520773e2e88
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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